(2R)-3-[2-[(1S,2R,4aR,6S,8aR)-6-hydroxy-1,2,4a-trimethyl-5-methylidene-3,4,6,7,8,8a-hexahydro-2H-naphthalen-1-yl]ethyl]-2-hydroxy-2H-furan-5-one

Details

• Internal ID: 8db5d272-a15a-4594-9676-096ae95923f4
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Diterpene lactones
• IUPAC Name: (2R)-3-[2-[(1S,2R,4aR,6S,8aR)-6-hydroxy-1,2,4a-trimethyl-5-methylidene-3,4,6,7,8,8a-hexahydro-2H-naphthalen-1-yl]ethyl]-2-hydroxy-2H-furan-5-one
• InChI: InChI=1S/C20H30O4/c1-12-7-9-20(4)13(2)15(21)5-6-16(20)19(12,3)10-8-14-11-17(22)24-18(14)23/h11-12,15-16,18,21,23H,2,5-10H2,1,3-4H3/t12-,15+,16-,18-,19+,20+/m1/s1
• InChI Key: QLIQMMRUUKMPEX-MOSDKIRPSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₃₀O₄
• Molecular Weight: 334.40 g/mol
• Exact Mass: 334.21440943 g/mol
• Topological Polar Surface Area (TPSA): 66.80 Ų
• XlogP: 3.30
• Atomic LogP (AlogP): 3.34
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9893	98.93%
Caco-2	+	0.5885	58.85%
Blood Brain Barrier	+	0.5500	55.00%
Human oral bioavailability	-	0.5000	50.00%
Subcellular localzation	Mitochondria	0.6345	63.45%
OATP2B1 inhibitior	-	0.8658	86.58%
OATP1B1 inhibitior	+	0.8374	83.74%
OATP1B3 inhibitior	+	0.8418	84.18%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.7250	72.50%
BSEP inhibitior	-	0.8878	88.78%
P-glycoprotein inhibitior	-	0.7028	70.28%
P-glycoprotein substrate	-	0.7677	76.77%
CYP3A4 substrate	+	0.6268	62.68%
CYP2C9 substrate	-	0.7981	79.81%
CYP2D6 substrate	-	0.8875	88.75%
CYP3A4 inhibition	+	0.5663	56.63%
CYP2C9 inhibition	-	0.8934	89.34%
CYP2C19 inhibition	-	0.8321	83.21%
CYP2D6 inhibition	-	0.9605	96.05%
CYP1A2 inhibition	-	0.7750	77.50%
CYP2C8 inhibition	-	0.7545	75.45%
CYP inhibitory promiscuity	-	0.8653	86.53%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.5528	55.28%
Eye corrosion	-	0.9932	99.32%
Eye irritation	-	0.8967	89.67%
Skin irritation	+	0.7082	70.82%
Skin corrosion	-	0.9225	92.25%
Ames mutagenesis	-	0.7400	74.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4527	45.27%
Micronuclear	-	0.8800	88.00%
Hepatotoxicity	+	0.5853	58.53%
skin sensitisation	-	0.7936	79.36%
Respiratory toxicity	+	0.5556	55.56%
Reproductive toxicity	+	0.9333	93.33%
Mitochondrial toxicity	+	0.9750	97.50%
Nephrotoxicity	-	0.5753	57.53%
Acute Oral Toxicity (c)	I	0.6665	66.65%
Estrogen receptor binding	+	0.8236	82.36%
Androgen receptor binding	+	0.5470	54.70%
Thyroid receptor binding	+	0.6889	68.89%
Glucocorticoid receptor binding	+	0.7863	78.63%
Aromatase binding	+	0.6716	67.16%
PPAR gamma	-	0.5682	56.82%
Honey bee toxicity	-	0.7323	73.23%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.5800	58.00%
Fish aquatic toxicity	+	0.9954	99.54%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL253	P34972	Cannabinoid CB2 receptor	98.47%	97.25%
CHEMBL2581	P07339	Cathepsin D	92.87%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	92.16%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	92.07%	97.09%
CHEMBL218	P21554	Cannabinoid CB1 receptor	89.95%	96.61%
CHEMBL226	P30542	Adenosine A1 receptor	89.30%	95.93%
CHEMBL4803	P29474	Nitric-oxide synthase, endothelial	85.73%	86.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	85.61%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.34%	95.56%
CHEMBL1994	P08235	Mineralocorticoid receptor	83.43%	100.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.60%	95.89%
CHEMBL1871	P10275	Androgen Receptor	82.20%	96.43%
CHEMBL1293249	Q13887	Kruppel-like factor 5	81.82%	86.33%
CHEMBL1902	P62942	FK506-binding protein 1A	80.76%	97.05%

Plants that contains it

• Callicarpa americana

Cross-Links

• PubChem: 44420767
• LOTUS: LTS0036522
• wikiData: Q105223604